The Traveling Philosopher's Guide to Accommodations

"Where do you recommend I stay?" This is one of the most frequently asked questions I receive. As someone who is neither an extreme budget traveler, nor luxury traveler, I find myself walking down a middle road. In the last 12 months, I've stayed in everything from a motel to bed and breakfast to luxury hostel to condo to cabana to luxury hotel to someone's house. There have been different factors that have gone into booking, such as convenience, price, WiFi availability, and how long I would actually be staying at the accommodations. For example, I spent much more time in the hotel at the Hyatt Regency in Jacksonville than I stayed in the person's Airbnb apartment in San Francisco.

So to help travelers navigate the ever-changing waters of booking accommodations, I've come up with this guide.


This can often be the most overwhelming part of finding accommodations. How far in advance should I book a hotel room? What amenities do I need? Should I use an online travel agency or even a travel agent to book? With so many questions, you can see why it can get so overwhelming.

I have a handful of online travel agency websites I use on a regular basis to book travel. For hotels, this includes Hipmunk, Orbitz, HotwirePriceline, and Expedia. I'll then compare those prices to what's listed on the hotel's website. Lastly, I'll call the hotel. Sometimes they have discounts or rates that aren't listed on the website. I'll especially do this if it's a trip coming up soon. If it's really last minute, I recommend Hotel Tonight, which is a hotel app that offers same-day hotel rates with as much as a 70% discount.

It's important to note that while online travel agencies feature most hotels, they don't feature all of them, such as many independently owned or boutique hotels, which are often my favorite hotels. In this case, you'll have to be a little more intensive in your research.

Mystery Accommodations

These types of accommodations that I'm about to talk about are not for everyone. Why, you ask? Well because you don't actually know which hotel you're staying at until you've reserved it. I use Priceline and Hotwire to do this. On Priceline, it's called "Name Your Own Price". You get to name a price you would like to pay, but you can only select a general neighborhood and hotel star. This can provide a significant discount if it's accepted, but like I mentioned, you won't know which hotel it is until your card has been charged. I did this last year in Jacksonville, Florida, having a rate of $65 accepted for the Hyatt Regency, which typically would have been over $150.

Hotwire has something similar called "Hotwire Hot Rates", except they show the price, rating, general neighborhood, and comparable hotels, but you don't know what hotel it is until you've booked it. To give you a better idea of prices and hotels when using these services by Priceline and Hotwire, I recommend using is a public forum in which travelers post successful rates/hotels they've gotten on Priceline and Hotwire. This doesn't guarantee you'll get the same hotel for the same price, but it can aid in your research to determine if it's worth it.

Bed and Breakfasts

Bed and breakfasts are often my favorite type of accommodations. I'm of the opinion that a bed and breakfast provides the most bang for your buck. While you may be paying more than some hotel rooms, you have a higher quality experience. Bed and breakfasts typically have free wireless Internet access, complimentary deluxe breakfast, and complimentary drinks and snacks. This is compared to many hotels that may charge for Internet access and have food items, but at a price, and often a price that is double, triple, or quadruple the price of the same items in grocery stores. While you can find most bed and breakfasts doing a Google search, I recommend using Select Registry or You aren't likely to find the same types of slashes in prices like you may find with Hotwire or Priceline for hotels, but bed and breakfasts often have mid-week and off-season specials.

Daily Deal Websites

Daily deal websites have continued to grow as an alternative for people that want heavily discounted items on restaurants, attractions, and more. The travel offerings of many of these websites have continued to grow, with some of them even offering packages that include airfare. Those travelers who like staying in a bed and breakfast or boutique hotel may prefer websites like LivingSocial and Groupon, since these are often your best chance of getting a steeply discounted rate from these types of accommodations. Daily deal websites allow you to book for a future date, but I highly recommend reading the fine print since there can be a lot of limitations. Travelzoo's Top 20 is a weekly alert I also subscribe to, which includes other types of travel deals beyond just hotels.

Alternative Accommodations

Everything else falls under "alternative accommodations". This includes guest homes, vacation rentals, glamping, tree houses, yurts, and Airbnb. I recommend this type of lodging for the person who is traveling on a budget and just needs the bare essentials. I often use websites like Airbnb or Roomorama because while I may often be staying in a spare room in someone's apartment, I'm not there long enough to justify having a hotel room. I'm predominantly there just to sleep, shower, and have breakfast. Some of the places I've stayed at on Airbnb have been as low as $30 per night and have included my own bedroom, but a shared bathroom. For a more curated list of these types of accommodations, take a look at Tripping.

Every once in a while I'll stay at what's typically being billed as a luxury hostel. However, in general, I don't couch surf or stay at hostels. It's more out of personal preference than anything. I've actually stayed at the StayON Beverly in Los Angeles more than any other place. While it's called a luxury hostel, I think of it more as a guest house, as it doesn't have the same ambiance of the typical hostel, but instead somewhat of a haven for the budget traveler, with shared bathrooms and quiet open spaces, but private rooms. Nonetheless, if you don't mind the hostel experience, then you may want to look at a hostel booking engine like or Hostelworld.

What are your accommodations of choice?